EP3019012A1 - Utilisation de pyridonecarboxamides sélectionnés ou de leurs sels en tant que substances actives pour lutter contre le stress abiotique des végétaux - Google Patents

Utilisation de pyridonecarboxamides sélectionnés ou de leurs sels en tant que substances actives pour lutter contre le stress abiotique des végétaux

Info

Publication number
EP3019012A1
EP3019012A1 EP14737209.8A EP14737209A EP3019012A1 EP 3019012 A1 EP3019012 A1 EP 3019012A1 EP 14737209 A EP14737209 A EP 14737209A EP 3019012 A1 EP3019012 A1 EP 3019012A1
Authority
EP
European Patent Office
Prior art keywords
substituted
unsubstituted
alkyl
alkoxy
haloalkoxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP14737209.8A
Other languages
German (de)
English (en)
Inventor
Lars ARVE
Frank Ziemer
Dirk Schmutzler
Jan Dittgen
Ines Heinemann
Martin Jeffrey Hills
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Priority to EP14737209.8A priority Critical patent/EP3019012A1/fr
Publication of EP3019012A1 publication Critical patent/EP3019012A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the invention relates to substituted pyridone carboxamides and their analogues, to processes for their preparation and to their use for increasing the stress tolerance in plants to abiotic stress, in particular for strengthening the
  • Plant growth and / or increase the plant yield Plant growth and / or increase the plant yield.
  • EP-A-544151 describes the effect of hydroxy-substituted pyridone carboxamides as herbicides.
  • EP 1 987 717 describes selected pyridone derivatives and their use as safeners, i. for the reduction of phytotoxic effects of agrochemicals, in particular of herbicides, on useful plants.
  • WO2001 / 14339 describes selected heterocyclic aromatic amides and their fungicidal action.
  • WO2013 / 037955 describes the use of compounds from the group of acylsulfonamides, in particular N- [4- (cyclopropylcarbamoyl) phenylsulfonyl] -2-methoxybenzamide (Cyprosulfamide) to increase the yield in crops, either alone or in combination with drugs of different classes of agents.
  • Pyridone carboxamides are mentioned in generic form as possible mixing partners.
  • representatives with pharmacological properties are known.
  • WO 2001/0551 15 discloses nicotinanilides as inducers of apoptosis, in US 2004/01 16479 dialkylnicotinamides as inhibitors of angiogenesis and in JP 2007186434
  • EP-A-522392 describes 6-trifluoromethyl-substituted pyridone carboxamides as precursors for the synthesis of herbicidally active sulfonylureas.
  • N-benzyl-5,6-dimethyl-2-oxo-dihydropyridine-3-carboxamide is described as a reaction product.
  • a use of such compounds to increase the tolerance to abiotic, not by pesticides, preferably not caused by herbicides stress in plants is not yet known.
  • abiotic stress defense reactions e.g., cold, heat, drought, salt, flooding
  • signal transduction chains e.g., transcription factors, kinases, phosphatases
  • the signal chain genes of the abiotic stress reaction include, among others.
  • Late Embryogenesis Abundant Proteins which include dehydrins as an important class, is known (Ingram and Bartels, 1996, Annu Rev Plant Physiol Plant Mol Biol 47: 277-403, Close, 1997, Physiol Plant 100: 291-296). These are chaperones, the vesicles, proteins and
  • HSF Heat Shock Factors
  • HSP Heat Shock Proteins
  • Substances or their stable synthetic derivatives and derived structures are also effective in external application to plants or seed dressing and activate defense reactions that result in an increased stress or pathogen tolerance of the plant [Sembdner, and Parthier, 1993, Ann. Rev. Plant Physiol. Plant Mol. Biol. 44: 569-589]. It is also known that chemical substances can increase the tolerance of plants to abiotic stress. Such substances are applied either by seed dressing, by foliar spraying or by soil treatment. Thus, increasing the abiotic stress tolerance of crops by treatment with systemic acquired resistance (SAR) or
  • SAR systemic acquired resistance
  • osmolytes e.g. Glycine betaine or its biochemical precursors, e.g. Choline derivatives have been observed (Chen et al., 2000, Plant Cell Environ 23: 609-618, Bergmann et al., DE-4103253). Also, the effect of antioxidants, e.g.
  • Naphtols and xanthines for increasing the abiotic stress tolerance in plants have already been described (Bergmann et al., DD-277832, Bergmann et al., DD-277835).
  • the molecular causes of the anti-stress effects of these substances are largely unknown.
  • PARP poly-ADP-ribose polymerases
  • PARG poly (ADP-ribose) glycohydrolases
  • plants have a number of endogenous reaction mechanisms that can effect effective defense against a variety of harmful organisms and / or natural abiotic stress.
  • the object of the present invention was to provide further compounds that increase the tolerance to natural, ie not by pesticides, preferably not triggered by herbicides abiotic stress in plants.
  • the present invention accordingly provides for the use of substituted pyridone carboxamides of the general formula (I) or salts thereof
  • R 1 is (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) -haloalkyl, ( C 2 -C 6 ) -
  • R 2 is (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) -
  • R 3 and R 4 independently of one another are hydrogen, (C 1 -C 16) -alkyl, (C 2 -C 16) -alkenyl or (C 2 -C 16) -alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or halogen by one or more radicals , Hydroxy, cyano, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkylthio, (C 1 -C 4 ) -alkylamino, and di [(C 1 -C 4) -alkyl] -amino , Hydroxycarbonyl, [(C 1 -C 4 ) -alkoxy] -carbonyl, [(C 1 -C 4 ) -haloalkoxy] -carbonyl, (C 3 -C 6) -cycloalkyl which
  • Phenyl which is unsubstituted or substituted heteroaryl which is unsubstituted or substituted and heterocyclyl which is unsubstituted or substituted, or
  • R 3 is hydrogen or (C 1 -C 6) -alkyl
  • R 4 is (Ci-C 6) -alkyl, (Ci-Ce) alkoxy, (C2-C6) alkenyloxy, (C 2 -C 6) alkynyloxy or (C 2 -C 6) - haloalkoxy or (C -C 6 ) -alkyl-SO 2 , or
  • R 3 and R 4 together with the directly bound N atom represent an amino acid residue, namely the naturally occurring in their racemic and in their respective D and L form, or R 3 and R 4 together with the directly bonded N atom form a four- to eight-membered heterocyclic ring which, in addition to the N atom, may also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group consisting of N, O and S, and unsubstituted or substituted by one or more radicals from the group halogen, cyano, nitro, (Ci-C 4) alkyl, (Ci-C4) - haloalkyl, (Ci-C 4) alkoxy, (Ci-C 4) - Haloalkoxy, hydroxycarbonyl, [(C 1 -C 4 ) -alkoxy] -carbonyl and (C 1 -C 4 ) -alkylthio, or
  • R 5 is hydrogen or (C 1 -C 6) -alkyl
  • R 6 and R 7 independently of one another denote hydrogen or (C 1 -C 6 ) -alkyl, or R 6 ,
  • R 7 together with the directly attached N atom form a five- to seven-membered, preferably saturated heterocyclic ring, such as, for example, piperidinyl, pyrrolidinyl or morpholinyl.
  • the compounds of the formula (I) also include tautomers which can be formed by hydrogen displacement and which structurally formally do not fall under the formula (I). Nevertheless, these tautomers are considered to be encompassed by the definition of the compounds of the formula (I) according to the invention.
  • the definition of the compounds of formula (I) includes the tautomeric structures of
  • R 1 , R 2 , R 3 and R 4 are as defined in formula (I). Preference is given to the use according to the invention of compounds of the general formula (I) or salts thereof, in which
  • R 1 is (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 3 -C 6 ) -cycloalkyl, (C 1 -C 6 ) -alkoxy or (C 1 -C 6 ) -haloalkoxy,
  • R 2 is (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C 3 -C 6) cycloalkyl, (Ci-C 6) alkoxy, (Ci-C6) - haloalkoxy or halogen and
  • R 3 and R 4 independently of one another are hydrogen, (C 1 -C 16) -alkyl, (C 2 -C 16) -alkenyl or (C 2 -C 16) -alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or halogen by one or more radicals , Hydroxy, cyano, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkylthio, (C 1 -C 4 ) -alkylamino, and di [(C 1 -C 4) -alkyl] -amino , Hydroxycarbonyl, [(C 1 -C 4 ) -alkoxy] -carbonyl, [(C 1 -C 4 ) -haloalkoxy] -carbonyl, (C 3 -C 6) -cycloalkyl which
  • Phenyl which is unsubstituted or substituted heteroaryl which is unsubstituted or substituted and heterocyclyl which is unsubstituted or substituted, or
  • R 3 is hydrogen or (C 1 -C 6) -alkyl
  • R 4 is (Ci-C 6) -alkyl, (Ci-Ce) alkoxy, (C2-C6) alkenyloxy, (C 2 -C 6) alkynyloxy or (C 2 -C 6) - haloalkoxy or (C -C 6 ) -alkyl-SO 2 , or
  • R 3 and R 4 together with the directly bound N atom represent an amino acid residue, namely the naturally occurring in their racemic and in their respective D and L form, or
  • heterocyclic ring which may contain, in addition to the N atom, also further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S, and unsubstituted or substituted by one or more radicals from the group halogen, cyano, nitro, ( Ci-C 4) alkyl, (Ci-C4) - haloalkyl, (Ci-C 4) alkoxy, (Ci-C 4) -haloalkoxy, hydroxycarbonyl, [(Ci-C 4) alkoxy] - carbonyl and (Ci-C 4 ) -Alkylthio is substituted or
  • R 5 is hydrogen or (C 1 -C 6 ) -alkyl
  • R 6 and R 7 independently of one another denote hydrogen or (C 1 -C 6 ) -alkyl, or R 6 and R 7 together with the directly bonded N atom form a five-bissile-membered, preferably saturated heterocyclic ring, for example piperidinyl, pyrrolidinyl or morpholinyl ,
  • R 1 is (C 1 -C 6 ) -alkyl or (C 1 -C 6 ) -haloalkyl
  • R 2 is (C 1 -C 6 ) -alkyl or halogen
  • R 3 and R 4 independently of one another are hydrogen, (C 1 -C 16) -alkyl, (C 2 -C 16) -alkenyl or (C 2 -C 16) -alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or halogen by one or more radicals , Hydroxy, cyano, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkylthio, (C 1 -C 4 ) -alkylamino, and di [(C 1 -C 4) -alkyl] -amino , Hydroxycarbonyl, [(C 1 -C 4 ) -alkoxy] -carbonyl, [(C 1 -C 4 ) -haloalkoxy] -carbonyl, (C 3 -C 6) -cycloalkyl which
  • heterocyclic ring which may contain, in addition to the N atom, also further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S, and unsubstituted or substituted by one or more radicals from the group halogen, cyano, nitro, ( C 1 -C 4 -alkyl, (C 1 -C 4 ) -
  • Haloalkyl (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, hydroxycarbonyl, [(C 1 -C 4 ) -alkoxy] -carbonyl and (C 1 -C 4 ) -alkylthio, or R 3 and R 4 together with the directly attached N atom, the group
  • R 5 is hydrogen or (Ci-C 6 ) alkyl
  • R 6 and R 7 independently of one another denote hydrogen or (C 1 -C 6 ) -alkyl, or R 6 ,
  • R 7 together with the directly attached N atom form a five- to seven-membered, preferably saturated heterocyclic ring, such as, for example, piperidinyl, pyrrolidinyl or morpholinyl.
  • R 1 is (C 1 -C 6 ) -alkyl or (C 1 -C 6 ) -haloalkyl
  • R 2 is (C 1 -C 6 ) -alkyl or halogen
  • R 3 and R 4 are each independently hydrogen, (C 1 -C 16) -alkyl , (C 2 -C 16) -alkenyl or (C 2 -C 16) -alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxy, cyano, (C 1 -C 4) -alkoxy, (Ci -C) haloalkoxy, (Ci-C) alkylthio, (Ci-C) alkylamino, di [(CI-C 4) -alkyl] amino, [(Ci-C 4) -alkoxy] carbonyl, [ (C 1 -
  • Phenyl which is unsubstituted or substituted heteroaryl which is unsubstituted or substituted and heterocyclyl which is unsubstituted or substituted, or
  • R 3 is hydrogen or (Ci-Ce) alkyl
  • R 4 is (Ci-C 6) -alkyl, (Ci-C 6) alkoxy, (C2-C6) alkenyloxy, (C 2 -C 6) alkynyloxy or (C 2 -C 6) - haloalkoxy, or ( Ci-C 6 ) -alkyl-SO 2 means or
  • R 3 and R 4 together with the directly bound N atom represent an amino acid residue, namely the naturally occurring in their racemic and in their respective D and L form, or
  • Hetero ring atoms preferably up to two further hetero ring atoms from the group N, O and S may contain and unsubstituted or by one or more radicals from the group halogen, cyano, nitro, (Ci-C 4 ) alkyl, (Ci-C 4 ) - Haloalkyl, (Ci-C) -alkoxy, (Ci-C) -haloalkoxy, [(Ci-C) -alkoxy] -carbonyl and (Ci-C) -alkylthio is substituted.,
  • substituted pyridone carboxamides of the general formula (I) or salts thereof
  • carbocyclic ring is condensed, or (C 4 -C 6) -cycloalkenyl which is fused on one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring,
  • Phenyl which is unsubstituted or substituted, heteroaryl which is unsubstituted or substituted or heterocyclyl which is unsubstituted or substituted, and
  • carbocyclic ring is condensed, or (C 4 -C 6) -cycloalkenyl which is fused on one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring,
  • Phenyl which is unsubstituted or substituted heteroaryl which is unsubstituted or substituted or heterocyclyl which is unsubstituted or substituted, or
  • R 3 is hydrogen or (C 1 -C 6) -alkyl
  • R 4 is (Ci-C 6) -alkyl, (Ci-Ce) alkoxy, (C2-C6) alkenyloxy, (C 2 -C 6) alkynyloxy or (C 2 -C 6) - haloalkoxy or (C -C 6 ) -alkyl-SO 2 , or
  • R 3 and R 4 together with the directly bound N atom represent an amino acid residue, namely the naturally occurring in their racemic and in their respective D and L form, or
  • heterocyclic ring which may contain, in addition to the N atom, also further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S, and unsubstituted or substituted by one or more radicals from the group halogen, cyano, nitro, ( Ci-C 4) alkyl, (Ci-C4) - haloalkyl, (Ci-C 4) alkoxy, (Ci-C 4) -haloalkoxy, hydroxycarbonyl, [(Ci-C 4) alkoxy] - carbonyl and (C 1 -C 4 ) -alkylthio, or
  • R 5 is hydrogen or (C 1 -C 6) -alkyl
  • R 6 and R 7 independently of one another denote hydrogen or (C 1 -C 6 ) -alkyl, or R 6 and R 7 together with the directly bonded N atom form a five- to seven-membered, preferably saturated heterocyclic ring, such as piperidinyl, pyrrolidinyl or Morpholinyl, except compounds of general formula (I), in which
  • R 1 and R 2 are methyl, R 3 is hydrogen and R 4 is benzyl, or
  • R 1 is (Ci-C 6) -alkyl or (Ci-C 6) -haloalkyl
  • R 2 is methyl
  • R 3 is hydrogen, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl or ( C 2 -C 6) alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, hydroxy, cyano, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (Ci -C) -alkylthio, (C 1 -C 4) -alkylamino, di [(C 1 -C 4) -alkyl] -amino, [(C 1 -C 4 ) -alkoxy] -carbonyl, [(C 1 -C 4 ) -haloalkoxy
  • Phenyl which is unsubstituted or substituted, hetaryl which is unsubstituted or substituted and heterocyclyl which is unsubstituted or substituted, and
  • R 4 is (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl or (C 2 -C 6) -alkynyl, wherein each of the
  • radicals being unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, cyano, (Ci-C 4) alkoxy, (Ci-C 4) haloalkoxy, (CI-C 4) -alkyl alkylthio, (Ci- C) -alkylamino, di [(C 1 -C 4) -alkyl] -amino, [(C 1 -C 4 ) -alkoxy] -carbonyl, [(C 1 -C 4 ) -haloalkoxy] -carbonyl, (C 3 -C 6) -cycloalkyl , Phenyl which is unsubstituted or substituted, heteroaryl which is unsubstituted or substituted, or heterocyclyl which is unsubstituted or substituted
  • Phenyl which is unsubstituted or substituted, hetaryl which is unsubstituted or substituted and heterocyclyl which is unsubstituted or substituted, or
  • R 3 is hydrogen or (C 1 -C 6) -alkyl
  • R 4 is (Ci-C 6) -alkyl, (Ci-Ce) alkoxy, (C2-C6) alkenyloxy, (C 2 -C 6) alkynyloxy or (C 2 -C 6) - haloalkoxy or (C -C 6 ) -alkyl-SO 2 , or
  • R 3 and R 4 together with the directly bound N atom represent an amino acid residue, namely the naturally occurring in their racemic and in their respective D and L form, or
  • R 1 is (C 1 -C 6 ) -alkyl or (C 1 -C 6 ) -haloalkyl
  • R 2 is ethyl
  • R 3 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl or (C 2 -C 6 ) -alkynyl,
  • each of the last-mentioned 3 radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, hydroxy, cyano, (C 1 -C 4 ) -alkoxy, (C 1 -C 6) -haloalkoxy, (C 1 -C 4 ) -alkylthio, ( C) -alkylamino, di [(Ci-C) -alkyl] -amino,
  • Phenyl which is unsubstituted or substituted, hetaryl which is unsubstituted or substituted and heterocyclyl which is unsubstituted or substituted, and
  • R 4 is (Ci-C 6) -alkyl, (Ci-Ce) alkoxy, (C2-C6) alkenyloxy, (C 2 -C 6) alkynyloxy or (C 2 -C 6) - haloalkoxy or (C -C 6 ) -alkyl-SO 2 , or
  • R 3 and R 4 together with the directly attached N atom represent an amino acid residue, namely the naturally occurring in their racemic and in their respective D and L form, or R 3 and R 4 together with the directly bonded N atom four - to
  • heterocyclic ring which may contain, in addition to the N atom, also further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S, and unsubstituted or substituted by one or more radicals from the group halogen, cyano, nitro, ( C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C -haloalkoxy, C 1 -C 4 -alkoxy-carbonyl and
  • substituted Pyridoncarboxamide the general formula (I) or salts thereof, wherein R 1 is (C 1 -C 6 ) -alkyl or (C 1 -C 6 ) -haloalkyl, R 2 is n-propyl,
  • R 3 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6) -alkenyl or (C 2 -C 6) -alkynyl,
  • each of the last-mentioned 3 radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, hydroxy, cyano, (C 1 -C 4 ) -alkoxy, (C 1 -C 6) -haloalkoxy, (C 1 -C 4 ) -alkylthio, ( C) -alkylamino, di [(C 1 -C 4 ) -alkyl] -amino, [(C 1 -C 4 ) -alkoxy] -carbonyl, [(C 1 -C 4 ) -haloalkoxy] -carbonyl, (C 3 -C 6) - Cycloalkyl, phenyl which is unsubstituted or substituted, heteroaryl which is unsubstituted or substituted, or heterocyclic which is unsubstituted or substituted, or denotes
  • Phenyl which is unsubstituted or substituted, hetaryl which is unsubstituted or substituted and heterocyclic which is unsubstituted or substituted, and
  • R 4 is (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl or (C 2 -C 6 ) -alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, hydroxy, cyano, (Ci-C 4) alkoxy, (Ci-C 4) haloalkoxy, (CI-C 4) -alkyl alkylthio, (Ci-C) alkylamino, di [(Ci-C) alkyl] -amino, [(C 1 -C 4 ) -alkoxy] -carbonyl, [(C 1 -C 4 ) -haloalkoxy] -carbonyl, (C 3 -C 6) -cycloalkyl, phenyl which is unsubstituted or substituted, heteroaryl which is unsub
  • heterocyclic ring which may contain, in addition to the N atom, also further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S, and unsubstituted or substituted by one or more radicals from the group halogen, cyano, nitro, ( C 1 -C 4 -alkyl, (C 1 -C 4 ) -
  • substituted Pyridoncarboxamide the general formula (I) or salts thereof, wherein
  • R 1 is (C 1 -C 6 ) -alkyl
  • R 2 is chlorine
  • R 3 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl or (C 2 -Cie) -alkynyl,
  • each of the last-mentioned 3 radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, hydroxy, cyano, (C 1 -C 4 ) -alkoxy, (C 1 -C 6) -haloalkoxy, (C 1 -C 4 ) -alkylthio, ( C) -alkylamino, di [(Ci-C) -alkyl] -amino, [(C 1 -C 4 ) -alkoxy] -carbonyl, [(C 1 -C 4 ) -haloalkoxy] -carbonyl, (C 3 -C 6) -cycloalkyl, phenyl which is unsubstituted or substituted, heteroaryl which is unsubstituted or substituted or Heterocyclyl, which is unsubstituted or substituted, means
  • Phenyl which is unsubstituted or substituted, hetaryl which is unsubstituted or substituted and heterocyclyl which is unsubstituted or substituted, and
  • R 4 is (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl or (C 2 -C 6 ) -alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, hydroxy, cyano, (Ci-C 4) alkoxy, (Ci-C 4) haloalkoxy, (CI-C 4) -alkyl alkylthio, (Ci-C) alkylamino, di [(Ci-C) alkyl] -amino, [(C 1 -C 4 ) -alkoxy] -carbonyl, [(C 1 -C 4 ) -haloalkoxy] -carbonyl, (C 3 -C 6) -cycloalkyl, phenyl which is unsubstituted or substituted, heteroaryl which is unsub
  • heterocyclic ring which may contain, in addition to the N atom, also further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S, and unsubstituted or substituted by one or more radicals from the group halogen, cyano, nitro, ( C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, [(C 1 -C 4 ) -alkoxy] -carbonyl and (C 1 -C 4 ) -alkyl ) Alkylthio is substuted.
  • substituted Pyridoncarboxamide the general formula (I) or salts thereof, wherein
  • R 1 is (C 1 -C 6 ) -alkyl
  • R 2 is bromine
  • R 3 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl or (C 2 -C 6 ) -alkynyl,
  • each of the last-mentioned 3 radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, hydroxy, cyano, (C 1 -C 4 ) -alkoxy, (C 1 -C 6) -haloalkoxy, (C 1 -C 4 ) -alkylthio, ( C) -alkylamino, di [(Ci-C) -alkyl] -amino,
  • Phenyl which is unsubstituted or substituted, hetaryl which is unsubstituted or substituted and is heterocyclyl which is unsubstituted or substituted, or is hydrogen or (C 1 -C 6) -alkyl and
  • R 3 and R 4 together with the directly bound N atom represent an amino acid residue, namely the naturally occurring in their racemic and in their respective D and L form, or R 3 and R 4 together with the directly bonded N atom form a four - to
  • heterocyclic ring which may contain, in addition to the N atom, also further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S, and unsubstituted or substituted by one or more radicals from the group halogen, cyano, nitro, ( C 1 -C 4 -alkyl, (C 1 -C 4 ) - Haloalkyl, (Ci-C) alkoxy, (Ci-C) haloalkoxy, [(Ci-C) alkoxy] carbonyl
  • substituted Pyridoncarboxamide the general formula (I) or salts thereof, wherein
  • R 1 is (C 1 -C 6 ) -alkyl
  • R 2 is iodine
  • R 3 denotes hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl or (C 2 -C 6 ) -alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or by one or more radicals from the group Halogen, hydroxy, cyano, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkylthio, (C 1 -C 4 ) -alkylamino, di [(C 1 -C 4) -alkyl] amino, [(ci
  • Phenyl which is unsubstituted or substituted, hetaryl which is unsubstituted or substituted and heterocyclic which is unsubstituted or substituted, and
  • R 4 is (C 1 -C 6 ) -alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, hydroxy, cyano, (Ci-C 4) alkoxy, (Ci-C 4) haloalkoxy, (CI-C 4) -alkyl alkylthio, (Ci-C) alkylamino, di [(Ci-C) alkyl] -amino, [(C 1 -C 4 ) -alkoxy] -carbonyl, [(C 1 -C 4 ) -haloalkoxy] -carbonyl, (C 3 -C 6) -cycloalkyl, phenyl which is unsubstituted or substituted, heteroaryl which is unsubstituted or substitute
  • Phenyl which is unsubstituted or substituted, hetaryl which is unsubstituted or substituted and is heterocyclyl which is unsubstituted or substituted, or is hydrogen or (C 1 -C 6) -alkyl and
  • heterocyclic ring which may contain, in addition to the N atom, also further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S, and unsubstituted or substituted by one or more radicals from the group halogen, cyano, nitro, ( C 1 -C 4 -alkyl, (C 1 -C 4 ) -
  • Haloalkyl (C 1 -C 4) -alkoxy, (C 1 -C 4) -haloalkoxy, [(C 1 -C 4 ) -alkoxy] -carbonyl and (C 1 -C 4 ) -alkylthio.
  • a further subject of the invention is also a spray solution for
  • halogen means, for example, fluorine, chlorine, bromine or iodine. If the term is used for a remainder, then "halogen" means
  • a fluorine, chlorine, bromine or iodine atom for example, a fluorine, chlorine, bromine or iodine atom.
  • Alkyl means according to the invention a straight-chain or branched open-chain, saturated hydrocarbon radical which is optionally mono- or polysubstituted.
  • Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio or nitro groups, particular preference is given to fluorine, chlorine, bromine or iodine.
  • Fluoroalkyl means a straight-chain or branched open-chain, saturated and fluorine-substituted hydrocarbon radical, at least one fluorine atom being in one of the possible positions.
  • Perfluoroalkyl means a straight-chain or branched, open-chain, saturated and completely fluorine-substituted hydrocarbon radical, for example CF 3, CF 2 CF 3,
  • Partially fluorinated alkyl means a straight-chain or branched, saturated hydrocarbon which is monosubstituted or polysubstituted by fluorine, the corresponding fluorine atoms being present as substituents on one or more
  • Hydrocarbon chain can be located, such as. B. CHFCH3, CH2CH2F, CH2CH2CF3, CHF 2, CH 2 F, CHFCF2CF3
  • Partially fluorinated haloalkyl means a straight-chain or branched, saturated hydrocarbon which is represented by various halogen atoms having at least one Fluorine atom is substituted, all other optional halogen atoms are selected from the group fluorine, chlorine, bromine or iodine.
  • the corresponding halogen atoms may be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain.
  • Partially fluorinated haloalkyl also includes the
  • Haloalkyl, alkenyl and alkynyl mean the same or different
  • Perhaloalkyl such. CCI 3 , CCIF 2 , CFCI 2 , CF 2 CCIF 2 , CF 2 CCIFCF 3 ; Polyhaloalkyl such. CH 2 CHFCI, CF 2 CCIFH, CF 2 CBrFH, CH 2 CF 3 ;
  • perhaloalkyl also encompasses the term perfluoroalkyl
  • polyhaloalkyl also encompasses the terms partially fluorinated alkyl and partially fluorinated haloalkyl.
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl;
  • (C 1 -C 4 ) -alkyl denotes a short notation for alkyl having one to four carbon atoms corresponding to the range given for C atoms, ie the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl.
  • General alkyl radicals having a larger specified range of carbon atoms eg.
  • (Ci-C6) -alkyl accordingly also include straight-chain or branched
  • hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, even in assembled radicals, are lower
  • Alkyl radicals including in the assembled radicals such as alkoxy, haloalkyl, etc., mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i Hexyl and 1, 3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and 1, 4-dimethylpentyl; Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, wherein at least one double bond or triple bond is contained. Preference is given to radicals having a double bond or triple bond.
  • Alkenyl in particular also includes straight-chain or branched open-chain
  • Hydrocarbon radicals having more than one double bond such as 1, 3-butadienyl and 1, 4-pentadienyl, but also allenyl or cumulene radicals having one or more cumulative double bonds, such as allenyl (1, 2-propadienyl), 1, 2-butadienyl and 1,2,3-pentatrienyl.
  • Alkenyl means e.g. Vinyl, which may optionally be substituted by further alkyl radicals, e.g.
  • alkynyl also includes straight-chain or branched open-chain
  • Hydrocarbon radicals having more than one triple bond or having one or more triple bonds and one or more double bonds such as 1, 3-butatrienyl and 3-penten-1-yn-1-yl.
  • (C 2 -C 6) alkynyl means ethynyl, propargyl, 1-methyl-prop-2-yn-1-yl, 2-butynyl, 2-pentynyl or
  • 2-hexynyl preferably propargyl, but-2-yn-1-yl, but-3-yn-1-yl or
  • cycloalkyl means a carbocyclic saturated ring system preferably having 3-8 ring C atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system preferably having 4-8 C atoms, for example 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1, 3-cyclohexadienyl or 1, 4-cyclohexadienyl,
  • aryl means a mono-, bi- or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably optionally mono- or polysubstituted a radical from the group halogen, nitro, hydroxy, cyano, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalky
  • optionally substituted aryl also includes polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, wherein the
  • Binding site on the aromatic system is.
  • aryl is also encompassed by the term “optionally substituted phenyl”.
  • a heterocyclic radical or ring can be saturated, unsaturated or heteroaromatic and unsubstituted or, for example, with a radical selected from the group consisting of halogen, nitro, hydroxy, cyano, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) - Haloalkyl, (C 1 -C 4) -alkoxy, (C 1 -C 4) -haloalkoxy, (C 1 -C 4) -alkylthio, (C 1 -C 4) -alkylsulfoxy, (C 1 -C 4) -alkylsulfone, (C 1 -C 4) -alkylamino, Di [(C 1 -C 4) alkyl] amino, [(C 1 -C 4 ) alkoxy] carbonyl, [(C 1 -C 4 ) haloalkoxy] carbonyl, (C 3 -
  • Hydroxycarbonyl or hydroxycarbonyl- (C 1 -C 4 ) -alkyl it preferably contains one or more heteroatoms in the ring, preferably from the group N, O and S; it is an aliphatic heterocyclyl radical having 3 to 7 ring atoms or a heteroaromatic radical having 5 or 6 ring atoms and contains 1, 2 or 3
  • heterocyclic radical may be e.g. a heteroaromatic radical or ring (heteroaryl), e.g. a mono-, bi- or polycyclic aromatic system in which at least one ring contains one or more heteroatoms,
  • pyridyl pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, oxazolyl, furyl, pyrrolyl, pyrazolyl and imidazolyl, or is a partial or complete hydrogenated radical such as oxiranyl, oxetanyl, pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, morpholinyl, tetrahydrofuryl.
  • substituents for a substituted is a partial or complete hydrogenated radical such as oxiranyl, oxetanyl, pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, morpholinyl, tetrahydrofuryl.
  • Heterocyclic radical are the substituents mentioned below in question, in addition also oxo.
  • the oxo group may also be attached to the hetero ring atoms, which may exist in different oxidation states, e.g. at N and S, occur.
  • Alkoxy is an alkyl radical bonded via an oxygen atom
  • alkenyloxy is an alkynyl radical bonded via an oxygen atom
  • alkynyloxy is an alkynyl radical bound via an oxygen atom
  • cycloalkyloxy is a cycloalkyl radical bonded via an oxygen atom
  • cycloalkenyloxy is a cycloalkenyl radical bonded via an oxygen atom.
  • alkylthio alone or as part of a chemical group - represents straight-chain or branched S-alkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as, for example, methylthio, ethylthio, n-propylthio, isopropylthio, n- Butylthio, isobutylthio, sec-butylthio and tert-butylthio.
  • Alkenylthio represents an alkenyl radical bonded via a sulfur atom
  • alkynylthio represents an alkynyl radical bonded via a sulfur atom
  • cycloalkylthio represents a cycloalkyl radical bonded via a sulfur atom
  • cycloalkenylthio represents a cycloalkenyl radical bonded via a sulfur atom
  • AI kylsulfinyl - alone or as part of a chemical group - kylsulfinyl straight or branched Al, preferably having 1 to 8, or having 1 to 6 carbon atoms such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl , Isobutylsulfinyl, sec-butylsulfinyl and tert-butylsulfinyl.
  • Al kylsulfonyl alone or as part of a chemical group - is straight-chain or branched alkylsulfonyl, preferably having 1 to 8, or having 1 to 6 carbon atoms such as methylsulfonyl,
  • cycloalkylsulfonyl alone or as part of a chemical group - is optionally substituted Cycloalkylsulfonyl, preferably having 3 to 6 carbon atoms such as cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl or cyclohexylsulfonyl.
  • arylsulfonyl is optionally substituted phenylsulfonyl or optionally substituted polycyclic arylsulfonyl, for example substituted by halogen, alkyl, haloalkyl, haloalkoxy or alkoxy groups.
  • the term “sulfilimine” means a group having a nitrogen-sulfur double bond in which nitrogen and sulfur are further substituted, the nitrogen atom preferably by a further substituted carbonyl group and the sulfur preferably by two identical or mixed alkyl, aryl and
  • Cycloalkyl substituents for example in the form of an N- (di-n-butyl-sulfanylidene), N- (di-iso-propyl-sulfanyliden), N- (di-n-propyl-sulfanyliden), N- (di-n-pentyl -sulfanylidene), N- (diisobutylsulfanylidene), N- (cyclobutylisopropylsulfanylidene), N- (n-propylisopropylsulfanylidene), N- (cyclopropylisopropyl) sulfanylidene) or N- (iso-butylisopropylsulfanylidene) unit.
  • the compounds of the general formula (I) can exist as stereoisomers.
  • the possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the general formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. For example, are one or more asymmetric
  • Stereoisomers can be obtained from the resulting mixtures in the preparation by conventional separation methods.
  • the chromatographic separation can be carried out both on an analytical scale to determine the enantiomeric excess or the diastereomeric excess, as well as on a preparative scale for the preparation of test samples for the biological assay.
  • stereoisomers can be prepared by using stereoselective reactions using optically active
  • the invention thus relates also all stereoisomers, which comprises the general formula (I), but are not specified with their specific stereoform, and mixtures thereof.
  • Residue definitions apply both to the end products of the formula (I) and
  • crops refers to crops used as plants for the production of food, feed or for technical purposes.
  • the compounds of the general formula (I) can be prepared by, for example,
  • R 1 and R 2 are defined as in the compound of formula (I) to be prepared according to the above definition of the residue
  • R 3 and R 4 are defined as in the compound of formula (I) to be prepared according to the above definition of the radical, if appropriate in the presence of a carboxylic acid-activating reagent, for example ⁇ , ⁇ -carbonyldiimidazole (CDI), or of a dehydrating agent, for example dicyclohexylcarbodiimide (DCC), to give the compound of the formula (I) or a carboxylic ester of the general formula (IV)
  • a carboxylic acid-activating reagent for example ⁇ , ⁇ -carbonyldiimidazole (CDI), or of a dehydrating agent, for example dicyclohexylcarbodiimide (DCC)
  • R 1 and R 2 are defined as in the compound of the formula (I) to be prepared according to the above definition and "alkyl” is an alkyl radical, for example methyl or ethyl, with an amine of the formula (III) or its salt,
  • R 3 and R 4 are as defined in the compound of formula (I) to be prepared according to the above definition, to give the compound of formula (I) or a carboxylic acid halide or anhydride of general formula (V),
  • R 1 and R 2 are as defined in the compound of formula (I) to be prepared according to the above definition and Hai is a halogen atom, for example Chlorine, or an acyloxy radical, with an amine of the formula (III) or its salt,
  • R 1 and R 2 are as defined in the compound of formula (I) to be prepared according to the above definition of the radical and "AI kyl” is an alkyl radical, for example methyl or ethyl,
  • the amide formations according to variant (a) can be carried out, for example, in an inert organic solvent in a temperature range between 0 ° C and 150 ° C, preferably 0 ° C and 50 ° C.
  • Suitable organic solvents are, for example, polar protic or aprotic solvents such as ethers, eg. As diethyl ether, tetrahydrofuran and dioxane, or nitriles such as acetonitrile, or amides such as dimethylformamide.
  • the amide formations according to variant (b) can be carried out, for example, in an inert organic solvent in a temperature range between 0 ° C and 150 ° C, preferably 50 ° C and 100 ° C.
  • Suitable organic solvents are, for example, polar protic or aprotic solvents such as ethers, z.
  • polar protic or aprotic solvents such as ethers, z.
  • the amide formations according to variant (c) can, for example, in the presence of an acid-binding agent in an inert organic solvent in a
  • Suitable organic solvents are, for example, polar protic or aprotic solvents such as ethers, eg. As diethyl ether, tetrahydrofuran and dioxane, or nitriles such as acetonitrile, or amides such as dimethylformamide.
  • polar protic or aprotic solvents such as ethers, eg. As diethyl ether, tetrahydrofuran and dioxane, or nitriles such as acetonitrile, or amides such as dimethylformamide.
  • Acid-binding agents are, for example, alkali metal or alkaline earth metal carbonates such as.
  • alkali metal or alkaline earth metal hydroxides such as sodium, potassium or calcium hydroxide
  • alkali metal hydrides or amides such as sodium or potassium hydride or amide
  • organic bases such as triethylamine, pyridine, dimethylaminopyridine, DBU (1,8-diazabicyclo [5.4.0] undec-7-ene), DBN (1,5-diazabicyclo [4.3.0] non-5-ene) and 1,4-diazabicyclo [2.2.2] octane ,
  • the malonamide may typically be converted to a reactive salt in an organic anhydrous polar protic or aprotic solvent, for example in an alcohol, with a strong base such as an alkali metal, alkali metal hydride or alkali metal alcoholate and then reacted with the compound of formula (VI).
  • an organic anhydrous polar protic or aprotic solvent for example in an alcohol
  • a strong base such as an alkali metal, alkali metal hydride or alkali metal alcoholate
  • Compound (VI) can be carried out usually in a temperature range between 0 ° C and the boiling point of the solvent (depending on the solvent about to 150 ° C).
  • the compounds of the formula (IV) in which R 2 is a halogen atom can be prepared by customary halogenations from the compounds of the formula (IVa). Chlorine (J. Org. Chem., 23, 1958, 1614), bromine (Synth., Commun., 19, 1989, 553-560, US Pat
  • the compounds of the general formula (IV) wherein R 1 and R 2 may be as in for the compound of formula (I) are defined according to the above radical definition of the compounds of the general formula (IVa) wherein R 1 and R 2 are as for the compound of formula (I) are defined according to the above residue definition, successively (by nitration BJ Med Chem 36, 1993, 2676-2688, J. Heterocycl Chem 33, 1996, 287-294), reduction (eg J. Med. Chem subsequent implementation of the diazonium salts by means of Sandmeyer directed. Schiemannn reaction are produced.
  • reaction mixture was treated with water and extracted with dichloromethane.
  • the org. Phases were washed with dil. Hydrochloric acid and water, dried and the solvents distilled off. 50.5 g (98% of theory) were obtained as a colorless oil.
  • reaction mixture was treated with water and extracted with dichloromethane.
  • the org. Phases were washed with dil. Hydrochloric acid and water, dried and the solvents distilled off. 75.7 g (88% of theory) were obtained as a colorless oil.
  • Methyl 5-chloro-6- [chloro (difluoro) methyl] -2-oxo-1,2-dihydropyridine-3-carboxylate (5.00 g, 18.4 mmol) was dissolved in 50 ml of methanol and treated with 50 ml of an aqueous solution of lithium hydroxide. Monohydrate (1 .16 g, 27.6 mmol) was added. The
  • Reaction mixture was stirred for 16 h at room temperature. After completion of the reaction, the reaction mixture under ice bath cooling with conc. Hydrochloric acid adjusted to pH 1-2, wherein a solid precipitated. This was sucked off, with water washed and dried for 2 h at 55 ° C in a vacuum. There was obtained 4.03 g (81% of theory) of a colorless solid.
  • numeric indices in the formula expressions are not subscripted in Table A, but arranged in the same row height and font size as the atomic symbols.
  • the formula CF 3 in the table is of the formula CF3 according to conventional notation subscripted or the formula CH 2 CH (CH2CH3) 2 of the formula CH 2 CH (CH 2 CH 3) 2 with subscripts.
  • NMR data of selected compounds mentioned in Table A above The NMR data of selected compounds listed in Table A are listed either in classical form ( ⁇ values, number of H atoms, multiplet splitting) or as NMR peak lists. The assignment of the mentioned in Table A.
  • the peak list therefore has the following form: ⁇ (intensity i); 82 (intensity.2); ; ⁇ , (intensity, ';; ⁇ ⁇ (intensity n )
  • the intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity can be shown compared to the most intense signal in the spectrum.
  • Tetramethylsilane and / or the chemical shift of the solvent used especially in the case of spectra, which are measured in DMSO. Therefore, the tetramethylsilane peak can occur in NMR peaks, but it does not have to.
  • Solvent peaks for example peaks of DMSO in DMSO- and the peak of water, which are usually of high intensity on average.
  • Impurities usually have on average a lower intensity than the peaks of the target compounds (for example with a purity of> 90%).
  • Such stereoisomers and / or impurities may be typical of the particular preparation process. Their peaks can thus help the reproduction of our manufacturing process by "by-product fingerprints".

Abstract

L'invention concerne l'utilisation de pyridonecarboxamides substitués de formule générale (I) ou de leurs sels, les restes dans la formule générale (I) correspondant aux définitions données dans la description, pour accroître la tolérance des végétaux au stress abiotique, pour renforcer leur croissance et/ou pour augmenter leur rendement. L'invention concerne en outre des procédés spéciaux de préparation des composés précités.
EP14737209.8A 2013-07-09 2014-07-07 Utilisation de pyridonecarboxamides sélectionnés ou de leurs sels en tant que substances actives pour lutter contre le stress abiotique des végétaux Withdrawn EP3019012A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP14737209.8A EP3019012A1 (fr) 2013-07-09 2014-07-07 Utilisation de pyridonecarboxamides sélectionnés ou de leurs sels en tant que substances actives pour lutter contre le stress abiotique des végétaux

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP13175770 2013-07-09
PCT/EP2014/064406 WO2015004040A1 (fr) 2013-07-09 2014-07-07 Utilisation de pyridonecarboxamides sélectionnés ou de leurs sels en tant que substances actives pour lutter contre le stress abiotique des végétaux
EP14737209.8A EP3019012A1 (fr) 2013-07-09 2014-07-07 Utilisation de pyridonecarboxamides sélectionnés ou de leurs sels en tant que substances actives pour lutter contre le stress abiotique des végétaux

Publications (1)

Publication Number Publication Date
EP3019012A1 true EP3019012A1 (fr) 2016-05-18

Family

ID=48782962

Family Applications (1)

Application Number Title Priority Date Filing Date
EP14737209.8A Withdrawn EP3019012A1 (fr) 2013-07-09 2014-07-07 Utilisation de pyridonecarboxamides sélectionnés ou de leurs sels en tant que substances actives pour lutter contre le stress abiotique des végétaux

Country Status (10)

Country Link
US (1) US20160150782A1 (fr)
EP (1) EP3019012A1 (fr)
JP (1) JP2016525510A (fr)
CN (1) CN105530814A (fr)
AR (1) AR096827A1 (fr)
AU (1) AU2014289341A1 (fr)
CA (1) CA2917559A1 (fr)
EA (1) EA201600097A1 (fr)
MX (1) MX2016000141A (fr)
WO (1) WO2015004040A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107698501A (zh) * 2017-10-25 2018-02-16 遵义医学院 5,6‑二甲基‑2‑羟基烟酸的制备工艺
CN111718292B (zh) * 2019-03-20 2023-05-02 鲁南制药集团股份有限公司 一种米力农中间体化合物
CN111718295B (zh) * 2019-03-20 2023-05-02 鲁南制药集团股份有限公司 一种高纯度米力农的制备方法
EP3994125A1 (fr) * 2019-07-02 2022-05-11 Regeneron Pharmaceuticals, Inc. Modulateurs de hsd17b13 et leurs procédés d'utilisation
CN111492978A (zh) * 2020-05-18 2020-08-07 广西八桂林木花卉种苗股份有限公司 一种大花序桉1212品种的组培快繁方法

Family Cites Families (184)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2532055A (en) 1945-04-03 1950-11-28 Wyeth Corp Pyridone derivatives
DE1905834C3 (de) 1969-02-06 1972-11-09 Basf Ag Verfahren zur Vermeidung des Staubens und Zusammenbackens von Salzen bzw.Duengemitteln
US4031105A (en) * 1974-07-20 1977-06-21 Laboratorios Hermes, S.A. 3-(N-2', 6'xylyl)-carboxamide pyridone-2
US4761373A (en) 1984-03-06 1988-08-02 Molecular Genetics, Inc. Herbicide resistance in plants
US5304732A (en) 1984-03-06 1994-04-19 Mgi Pharma, Inc. Herbicide resistance in plants
US5331107A (en) 1984-03-06 1994-07-19 Mgi Pharma, Inc. Herbicide resistance in plants
DE3534948A1 (de) 1985-10-01 1987-04-09 Bayer Ag Fungizide und wachstumsregulatorische mittel
US4960896A (en) 1985-11-26 1990-10-02 A. H. Robins Company, Inc. Process for the preparation of 5-chloro and 5-bromo-2-hydroxynicotinic acids
ES2018274T5 (es) 1986-03-11 1996-12-16 Plant Genetic Systems Nv Celulas vegetales resistentes a los inhibidores de glutamina sintetasa, preparadas por ingenieria genetica.
US5273894A (en) 1986-08-23 1993-12-28 Hoechst Aktiengesellschaft Phosphinothricin-resistance gene, and its use
US5276268A (en) 1986-08-23 1994-01-04 Hoechst Aktiengesellschaft Phosphinothricin-resistance gene, and its use
US5637489A (en) 1986-08-23 1997-06-10 Hoechst Aktiengesellschaft Phosphinothricin-resistance gene, and its use
US5378824A (en) 1986-08-26 1995-01-03 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
US5605011A (en) 1986-08-26 1997-02-25 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
US5013659A (en) 1987-07-27 1991-05-07 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
US5638637A (en) 1987-12-31 1997-06-17 Pioneer Hi-Bred International, Inc. Production of improved rapeseed exhibiting an enhanced oleic acid content
GB8810120D0 (en) 1988-04-28 1988-06-02 Plant Genetic Systems Nv Transgenic nuclear male sterile plants
US5084082A (en) 1988-09-22 1992-01-28 E. I. Du Pont De Nemours And Company Soybean plants with dominant selectable trait for herbicide resistance
US5201931A (en) 1988-12-01 1993-04-13 Her Majesty The Queen In Right Of Canada, As Represented By The National Research Council Of Canada Abscisic acid-related plant growth regulators - germination promoters
DD277835A1 (de) 1988-12-13 1990-04-18 Forschzent Bodenfruchtbarkeit Mittel zur erhoehung der stresstoleranz von kulturpflanzen
DD277832A1 (de) 1988-12-13 1990-04-18 Forschzent Bodenfruchtbarkeit Mittel zur erhoehung der stresstoleranz von kulturpflanzen
US6013861A (en) 1989-05-26 2000-01-11 Zeneca Limited Plants and processes for obtaining them
ES2161681T3 (es) 1989-08-10 2001-12-16 Aventis Cropscience Nv Plantas con flores modificadas.
US5908810A (en) 1990-02-02 1999-06-01 Hoechst Schering Agrevo Gmbh Method of improving the growth of crop plants which are resistant to glutamine synthetase inhibitors
US5739082A (en) 1990-02-02 1998-04-14 Hoechst Schering Agrevo Gmbh Method of improving the yield of herbicide-resistant crop plants
WO1991015578A1 (fr) 1990-04-04 1991-10-17 Pioneer Hi-Bred International, Inc. Production de graines de colza ameliorees presentant une teneur reduite en acides gras satures
US5198599A (en) 1990-06-05 1993-03-30 Idaho Resarch Foundation, Inc. Sulfonylurea herbicide resistance in plants
DK0536330T3 (da) 1990-06-25 2002-04-22 Monsanto Technology Llc Glyphosattolerante planter
FR2667078B1 (fr) 1990-09-21 1994-09-16 Agronomique Inst Nat Rech Sequence d'adn conferant une sterilite male cytoplasmique, genome mitochondrial, mitochondrie et plante contenant cette sequence, et procede de preparation d'hybrides.
DE4103253C2 (de) 1991-02-04 2000-03-23 Aua Agrar Und Umweltanalytik G Mittel zur Erhöhung der Streßtoleranz von land- und forstwirtschaftlichen Kulturpflanzen
DE4104782B4 (de) 1991-02-13 2006-05-11 Bayer Cropscience Gmbh Neue Plasmide, enthaltend DNA-Sequenzen, die Veränderungen der Karbohydratkonzentration und Karbohydratzusammensetzung in Pflanzen hervorrufen, sowie Pflanzen und Pflanzenzellen enthaltend dieses Plasmide
EP0502740B1 (fr) 1991-03-07 1998-05-27 E.I. Du Pont De Nemours And Company Pyridine sulfonamide herbicide
US5235060A (en) 1991-07-11 1993-08-10 E. I. Du Pont De Nemours And Company Certain three component ionic substituted pyridine compounds as intermediates for preparation as herbicides
US5731180A (en) 1991-07-31 1998-03-24 American Cyanamid Company Imidazolinone resistant AHAS mutants
DE4128828A1 (de) 1991-08-30 1993-03-04 Basf Ag Ammonium- oder harnstoffhaltige duengemittel und verfahren zu ihrer herstellung
US6270828B1 (en) 1993-11-12 2001-08-07 Cargrill Incorporated Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability
DE4138819A1 (de) * 1991-11-26 1993-05-27 Basf Ag Hydroxypyridoncarbonsaeureamide, deren herstellung und verwendung
DE4227061A1 (de) 1992-08-12 1994-02-17 Inst Genbiologische Forschung DNA-Sequenzen, die in der Pflanze die Bildung von Polyfructanen (Lävanen) hervorrufen, Plasmide enthaltend diese Sequenzen sowie Verfahren zur Herstellung transgener Pflanzen
GB9218185D0 (en) 1992-08-26 1992-10-14 Ici Plc Novel plants and processes for obtaining them
ES2217254T3 (es) 1992-10-14 2004-11-01 Syngenta Limited Nuevas plantas y procesos para obtenerlas.
GB9223454D0 (en) 1992-11-09 1992-12-23 Ici Plc Novel plants and processes for obtaining them
BR9406484A (pt) 1993-03-25 1996-01-09 Ciba Geigy Ag Novas proteinas e cepas pesticidas
JP3527242B2 (ja) 1993-04-27 2004-05-17 カージル，インコーポレーテッド 食用の非水素化カノラ油
WO1995004826A1 (fr) 1993-08-09 1995-02-16 Institut Für Genbiologische Forschung Berlin Gmbh Enzymes de deramification et sequences d'adn les codant, utilisables dans la modification du degre de ramification de l'amidon amylopectinique dans des plantes
DE4330960C2 (de) 1993-09-09 2002-06-20 Aventis Cropscience Gmbh Kombination von DNA-Sequenzen, die in Pflanzenzellen und Pflanzen die Bildung hochgradig amylosehaltiger Stärke ermöglichen, Verfahren zur Herstellung dieser Pflanzen und die daraus erhaltbare modifizierte Stärke
EP0675198A4 (fr) 1993-10-01 1996-01-10 Mitsubishi Chem Ind Gene identifiant un cytoplasme vegetal sterile et procede pour preparer un vegetal hybride a l'aide de celui-ci.
AU692791B2 (en) 1993-10-12 1998-06-18 Agrigenetics, Inc. Brassica napus variety AG019
KR960705938A (ko) 1993-11-09 1996-11-08 미리암 디. 메코너헤이 유전자 전환된 프럭탄 축적 작물 및 그의 제조 방법(Transgenic Fructan Accumulating Crops and Method for Their Production)
EP0754235A1 (fr) 1994-03-25 1997-01-22 National Starch and Chemical Investment Holding Corporation Procede pour produire une fecule modifiee a partir de plants de pommes de terre
JP3555086B2 (ja) 1994-05-18 2004-08-18 プランテック バイオテクノロジスク ゲーエムベーハー フォーシュング アンド エンテゥウィックラング 植物、真菌および微生物中で直鎖型α−１，４グルカンの合成を促進することができる酵素をコードするＤＮＡ配列
EP0802720A4 (fr) 1994-06-21 1999-01-13 Zeneca Ltd Nouvelles plantes et leur procede d'obtention
US5824790A (en) 1994-06-21 1998-10-20 Zeneca Limited Modification of starch synthesis in plants
NL1000064C1 (nl) 1994-07-08 1996-01-08 Stichting Scheikundig Onderzoe Produktie van oligosacchariden in transgene planten.
DE4441408A1 (de) 1994-11-10 1996-05-15 Inst Genbiologische Forschung DNA-Sequenzen aus Solanum tuberosum kodierend Enzyme, die an der Stärkesynthese beteiligt sind, Plasmide, Bakterien, Pflanzenzellen und transgene Pflanzen enhaltend diese Sequenzen
DE4447387A1 (de) 1994-12-22 1996-06-27 Inst Genbiologische Forschung Debranching-Enzyme aus Pflanzen und DNA-Sequenzen kodierend diese Enzyme
AU4634396A (en) 1995-01-06 1996-07-24 Centrum Voor Plantenveredelings- En Reproduktieonderzoek (Cpro - Dlo) Dna sequences encoding carbohydrate polymer synthesizing enzymes and method for producing transgenic plants
DE19509695A1 (de) 1995-03-08 1996-09-12 Inst Genbiologische Forschung Verfahren zur Herstellung einer modifizieren Stärke in Pflanzen, sowie die aus den Pflanzen isolierbare modifizierte Stärke
CZ331797A3 (cs) 1995-04-20 1998-06-17 American Cyanamid Company Produkty rezistentní na herbicidy vyvíjené na struktuře založeným způsobem
US5853973A (en) 1995-04-20 1998-12-29 American Cyanamid Company Structure based designed herbicide resistant products
WO1996034968A2 (fr) 1995-05-05 1996-11-07 National Starch And Chemical Investment Holding Corporation Ameliorations apportees a une composition a base d'amidon de plante
FR2734842B1 (fr) 1995-06-02 1998-02-27 Rhone Poulenc Agrochimie Sequence adn d'un gene de l'hydroxy-phenyl pyruvate dioxygenase et obtention de plantes contenant un gene de l'hydroxy-phenyl pyruvate dioxygenase, tolerantes a certains herbicides
US5712107A (en) 1995-06-07 1998-01-27 Pioneer Hi-Bred International, Inc. Substitutes for modified starch and latexes in paper manufacture
US6284479B1 (en) 1995-06-07 2001-09-04 Pioneer Hi-Bred International, Inc. Substitutes for modified starch and latexes in paper manufacture
GB9513881D0 (en) 1995-07-07 1995-09-06 Zeneca Ltd Improved plants
FR2736926B1 (fr) 1995-07-19 1997-08-22 Rhone Poulenc Agrochimie 5-enol pyruvylshikimate-3-phosphate synthase mutee, gene codant pour cette proteine et plantes transformees contenant ce gene
GB2305174A (en) 1995-09-15 1997-04-02 Zeneca Ltd Chemical process
DK0851934T3 (da) 1995-09-19 2006-07-31 Bayer Bioscience Gmbh Planter, som syntetiserer en modificeret stivelse, fremgangsmåder til deres fremstilling samt modificeret stivelse
GB9524938D0 (en) 1995-12-06 1996-02-07 Zeneca Ltd Modification of starch synthesis in plants
DE19601365A1 (de) 1996-01-16 1997-07-17 Planttec Biotechnologie Gmbh Nucleinsäuremoleküle aus Pflanzen codierend Enzyme, die an der Stärkesynthese beteiligt sind
DE19608918A1 (de) 1996-03-07 1997-09-11 Planttec Biotechnologie Gmbh Nucleinsäuremoleküle, die neue Debranching-Enzyme aus Mais codieren
US5773704A (en) 1996-04-29 1998-06-30 Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College Herbicide resistant rice
DE19618125A1 (de) 1996-05-06 1997-11-13 Planttec Biotechnologie Gmbh Nucleinsäuremoleküle, die neue Debranching-Enzyme aus Kartoffel codieren
DE19619918A1 (de) 1996-05-17 1997-11-20 Planttec Biotechnologie Gmbh Nucleinsäuremoleküle codierend lösliche Stärkesynthasen aus Mais
CZ389098A3 (cs) 1996-05-29 1999-02-17 Hoechst Schering Agrevo Gmbh Molekuly nukleové kyseliny kódující enzymy z pšenice účastnící se syntézy škrobu
WO1997047807A1 (fr) 1996-06-12 1997-12-18 Pioneer Hi-Bred International, Inc. Substituts de l'amidon modifie utilises dans la fabrication du papier
WO1997047808A1 (fr) 1996-06-12 1997-12-18 Pioneer Hi-Bred International, Inc. Substituts de l'amidon modifie utilises dans la fabrication du papier
CA2257621C (fr) 1996-06-12 2003-02-04 Pioneer Hi-Bred International, Inc. Substituts de l'amidon modifie utilises dans la fabrication du papier
AUPO069996A0 (en) 1996-06-27 1996-07-18 Australian National University, The Manipulation of plant cellulose
US5850026A (en) 1996-07-03 1998-12-15 Cargill, Incorporated Canola oil having increased oleic acid and decreased linolenic acid content
US5773702A (en) 1996-07-17 1998-06-30 Board Of Trustees Operating Michigan State University Imidazolinone herbicide resistant sugar beet plants
DE19631764A1 (de) 1996-08-06 1998-02-12 Basf Ag Neue Nitrifikationsinhibitoren sowie die Verwendung von Polysäuren zur Behandlung von Mineraldüngemitteln die einen Nitrifikationsinhibitor enthalten
GB9623095D0 (en) 1996-11-05 1997-01-08 Nat Starch Chem Invest Improvements in or relating to starch content of plants
US6232529B1 (en) 1996-11-20 2001-05-15 Pioneer Hi-Bred International, Inc. Methods of producing high-oil seed by modification of starch levels
DE19653176A1 (de) 1996-12-19 1998-06-25 Planttec Biotechnologie Gmbh Neue Nucleinsäuremoleküle aus Mais und ihre Verwendung zur Herstellung einer modifizierten Stärke
CA2193938A1 (fr) 1996-12-24 1998-06-24 David G. Charne Oleagineux du genre brassica renfermant un gene restaurateur de la fertilite ameliore encodant la sterilite male cytoplasmique ogura
US5981840A (en) 1997-01-24 1999-11-09 Pioneer Hi-Bred International, Inc. Methods for agrobacterium-mediated transformation
DE19708774A1 (de) 1997-03-04 1998-09-17 Max Planck Gesellschaft Nucleinsäuremoleküle codierend Enzyme die Fructosylpolymeraseaktivität besitzen
DE19709775A1 (de) 1997-03-10 1998-09-17 Planttec Biotechnologie Gmbh Nucleinsäuremoleküle codierend Stärkephosphorylase aus Mais
GB9718863D0 (en) 1997-09-06 1997-11-12 Nat Starch Chem Invest Improvements in or relating to stability of plant starches
DE19749122A1 (de) 1997-11-06 1999-06-10 Max Planck Gesellschaft Nucleinsäuremoleküle codierend Enzyme, die Fructosyltransferaseaktivität besitzen
FR2770854B1 (fr) 1997-11-07 2001-11-30 Rhone Poulenc Agrochimie Sequence adn d'un gene de l'hydroxy-phenyl pyruvate dioxygenase et obtention de plantes contenant un tel gene, tolerantes aux herbicides
FR2772789B1 (fr) 1997-12-24 2000-11-24 Rhone Poulenc Agrochimie Procede de preparation enzymatique d'homogentisate
AU3478499A (en) 1998-04-09 1999-11-01 E.I. Du Pont De Nemours And Company Starch r1 phosphorylation protein homologs
DE19820607A1 (de) 1998-05-08 1999-11-11 Hoechst Schering Agrevo Gmbh Nucleinsäuremoleküle codierend Enzyme aus Weizen, die an der Stärkesynthese beteiligt sind
DE19820608A1 (de) 1998-05-08 1999-11-11 Hoechst Schering Agrevo Gmbh Nucleinsäuremoleküle codierend Enzyme aus Weizen, die an der Stärkesynthese beteiligt sind
PL197407B1 (pl) 1998-05-13 2008-03-31 Bayer Bioscience Gmbh Komórka rośliny transgenicznej, roślina transgeniczna, sposób wytwarzania rośliny transgenicznej, materiał rozmnożeniowy rośliny, zastosowanie cząsteczek kwasu nukleinowego i sposób wytwarzania zmodyfikowanej skrobi
DE19821614A1 (de) 1998-05-14 1999-11-18 Hoechst Schering Agrevo Gmbh Sulfonylharnstoff-tolerante Zuckerrübenmutanten
AU758890B2 (en) 1998-06-15 2003-04-03 National Starch And Chemical Investment Holding Corporation Improvements in or relating to plants and plant products
US6693185B2 (en) 1998-07-17 2004-02-17 Bayer Bioscience N.V. Methods and means to modulate programmed cell death in eukaryotic cells
DE19836098A1 (de) 1998-07-31 2000-02-03 Hoechst Schering Agrevo Gmbh Pflanzen, die eine modifizierte Stärke synthetisieren, Verfahren zur Herstellung der Pflanzen, ihre Verwendung sowie die modifizierte Stärke
DE19836099A1 (de) 1998-07-31 2000-02-03 Hoechst Schering Agrevo Gmbh Nukleinsäuremoleküle kodierend für eine ß-Amylase, Pflanzen, die eine modifizierte Stärke synthetisieren, Verfahren zur Herstellung der Pflanzen, ihre Verwendung sowie die modifizierte Stärke
AU6018399A (en) 1998-08-25 2000-03-14 Pioneer Hi-Bred International, Inc. Plant glutamine: fructose-6-phosphate amidotransferase nucleic acids
CA2342124A1 (fr) 1998-09-02 2000-03-16 Planttec Biotechnologie Gmbh Molecules d'acide nucleique codant une amylosucrase
DE59915126D1 (de) 1998-10-09 2010-03-04 Bayer Bioscience Gmbh Nucleinsäuremoleküle codierend ein verzweigungsenzym aus bakterien der gattung neisseria sowie verfahren zur herstellung von alpha-1,6-verzweigten alpha-1,4-glucanen
DE19924342A1 (de) 1999-05-27 2000-11-30 Planttec Biotechnologie Gmbh Genetisch modifizierte Pflanzenzellen und Pflanzen mit erhöhter Aktivität eines Amylosucraseproteins und eines Verzweigungsenzyms
US6624139B1 (en) 1998-11-05 2003-09-23 Eden Bioscience Corporation Hypersensitive response elicitor-induced stress resistance
AU773808B2 (en) 1998-11-09 2004-06-10 Bayer Cropscience Aktiengesellschaft Nucleic acid molecules from rice and their use for the production of modified starch
US6531648B1 (en) 1998-12-17 2003-03-11 Syngenta Participations Ag Grain processing method and transgenic plants useful therein
DE19905069A1 (de) 1999-02-08 2000-08-10 Planttec Biotechnologie Gmbh Nucleinsäuremoleküle codierend Alternansucrase
US6323392B1 (en) 1999-03-01 2001-11-27 Pioneer Hi-Bred International, Inc. Formation of brassica napus F1 hybrid seeds which exhibit a highly elevated oleic acid content and a reduced linolenic acid content in the endogenously formed oil of the seeds
MXPA01010930A (es) 1999-04-29 2003-06-30 Syngenta Ltd Plantas resistentes a herbicidas.
IL146063A0 (en) 1999-04-29 2002-07-25 Marlow Foods Ltd Herbicide resistant plants
DE19926771A1 (de) 1999-06-11 2000-12-14 Aventis Cropscience Gmbh Nukleinsäuremoleküle aus Weizen, transgene Pflanzenzellen und Pflanzen und deren Verwendung für die Herstellung modifizierter Stärke
DE19937348A1 (de) 1999-08-11 2001-02-22 Aventis Cropscience Gmbh Nukleinsäuremoleküle aus Pflanzen codierend Enzyme, die an der Stärkesynthese beteiligt sind
DE19937643A1 (de) 1999-08-12 2001-02-22 Aventis Cropscience Gmbh Transgene Zellen und Pflanzen mit veränderter Aktivität des GBSSI- und des BE-Proteins
AU7647000A (en) 1999-08-20 2001-03-19 Basf Plant Science Gmbh Increasing the polysaccharide content in plants
HU228503B1 (hu) * 1999-08-20 2013-03-28 Dow Agrosciences Llc Gombaölõ heterociklusos aromás amidok, ezeket tartalmazó készítmények és eljárás alkalmazásukra
US6423886B1 (en) 1999-09-02 2002-07-23 Pioneer Hi-Bred International, Inc. Starch synthase polynucleotides and their use in the production of new starches
US6472588B1 (en) 1999-09-10 2002-10-29 Texas Tech University Transgenic cotton plants with altered fiber characteristics transformed with a sucrose phosphate synthase nucleic acid
GB9921830D0 (en) 1999-09-15 1999-11-17 Nat Starch Chem Invest Plants having reduced activity in two or more starch-modifying enzymes
AR025996A1 (es) 1999-10-07 2002-12-26 Valigen Us Inc Plantas no transgenicas resistentes a los herbicidas.
EP1257536A1 (fr) 2000-01-27 2002-11-20 Cytovia, Inc. Nicotinamides substituees, leurs analogues, activateurs des caspases et inducteurs de l'apoptose et leur emploi
US6822146B2 (en) 2000-03-09 2004-11-23 E. I. Du Pont De Nemours And Company Sulfonylurea-tolerant sunflower line M7
EP1261695B1 (fr) 2000-03-09 2005-06-22 Monsanto Technology LLC Procedes permettant de rendre des plantes tolerantes au glyphosate et compositions associees
BR0114322A (pt) 2000-09-29 2004-06-15 Syngenta Ltd Enzima de epsps resistente a glifosato, polinucleotìdeo isolado, vetor, material de plantas, plantas completas férteis, morfologicamente normais, soja, canola, brassica, algodão, beterraba sacarina, girassol, ervilhas, batatas e beterrabas de forragem, métodos para controlar seletivamente ervas daninhas em um campo, e para produzir plantas que sejam substancialmente tolerantes ou substancialmente resistentes a herbicida de glifosato, uso do polinucleotìdeo, métodos para selecionar material biológico transformado de modo a expressar um gene de interesse, e para regenerar uma planta fértil transformada para conter dna estranho, e, kit diagnóstico
US6734340B2 (en) 2000-10-23 2004-05-11 Bayer Cropscience Gmbh Monocotyledon plant cells and plants which synthesise modified starch
CN101684458A (zh) 2000-10-30 2010-03-31 弗迪亚股份有限公司 新的草甘膦n-乙酰转移酶(gat)基因
FR2815969B1 (fr) 2000-10-30 2004-12-10 Aventis Cropscience Sa Plantes tolerantes aux herbicides par contournement de voie metabolique
CN1326996C (zh) 2000-12-08 2007-07-18 联邦科学及工业研究组织 蔗糖合酶的基因表达在植物组织中的修饰及其用途
AU2002338233A1 (en) 2001-03-30 2002-10-15 Basf Plant Science Gmbh Glucan chain length domains
DE60226508D1 (de) 2001-06-12 2008-06-19 Bayer Cropscience Gmbh Transgene pflanzen die stärke mit hohem amylosegehalt herstellen
AU2002322435A1 (en) 2001-08-09 2003-02-24 Cibus Genetics Non-transgenic herbicide resistant plants
PL370416A1 (en) 2001-10-17 2005-05-30 Basf Plant Science, Gmbh Starch
DE10208132A1 (de) 2002-02-26 2003-09-11 Planttec Biotechnologie Gmbh Verfahren zur Herstellung von Maispflanzen mit erhöhtem Blattstärkegehalt und deren Verwendung zur Herstellung von Maissilage
AR039501A1 (es) 2002-04-30 2005-02-23 Verdia Inc Genes de glifosato n-acetil transferasa (gat)
FR2844142B1 (fr) 2002-09-11 2007-08-17 Bayer Cropscience Sa Plantes transformees a biosynthese de prenylquinones amelioree
US20040116479A1 (en) 2002-10-04 2004-06-17 Fortuna Haviv Method of inhibiting angiogenesis
CA2498511A1 (fr) 2002-10-29 2004-05-13 Basf Plant Science Gmbh Compositions et procedes permettant d'identifier des plantes presentant une meilleure tolerance aux herbicides imidazolinones
US20040110443A1 (en) 2002-12-05 2004-06-10 Pelham Matthew C. Abrasive webs and methods of making the same
PT1578973E (pt) 2002-12-19 2008-10-16 Bayer Cropscience Ag Células de plantas e plantas que sintetizam um amido com uma melhor viscosidade final
WO2004078983A2 (fr) 2003-03-07 2004-09-16 Basf Plant Science Gmbh Production d'amylose amelioree dans les plantes
BRPI0409363A (pt) 2003-04-09 2006-04-25 Bayer Bioscience Nv métodos e meios para o aumento da toleráncia de plantas a condições de tensão
MXPA05011585A (es) 2003-04-29 2006-05-25 Pioneer Hi Bred Int Genes de glifosato-n-acetil transferasa (gat) novedosos.
WO2005002359A2 (fr) 2003-05-22 2005-01-13 Syngenta Participations Ag Amidon modifie, ses utilisations, ses procedes de production
EP1633875B1 (fr) 2003-05-28 2012-05-02 Basf Se Plantes de ble presentant une tolerance accrue aux herbicides d'imidazolinone
EP1493328A1 (fr) 2003-07-04 2005-01-05 Institut National De La Recherche Agronomique Production des lignées B. napus double zéro restauratrices avec une bonne qualité agronomique
CN1833026A (zh) 2003-07-31 2006-09-13 东洋纺织株式会社 生产透明质酸的植物
BRPI0412944A (pt) 2003-08-15 2006-09-26 Commw Scient Ind Res Org processos e meios para alteração de caracterìsticas de fibra em plantas produzindo fibra
UY28495A1 (es) 2003-08-29 2005-03-31 Inst Nac De Tecnologia Agropec Plantas de arroz que tienen una mayor tolerancia a los herbicidas de imidazolinona
AR046090A1 (es) 2003-09-30 2005-11-23 Bayer Cropscience Gmbh Plantas con actividad aumentada de una enzima de ramificacion de la clase 3
EP1687417B9 (fr) 2003-09-30 2011-03-30 Bayer CropScience AG Vegetaux ayant une activite reduite de l'enzyme de ramification de classe 3
IN2004DE01799A (fr) 2003-10-23 2007-01-12 Bayer Cropscience Ag
DE10349502A1 (de) 2003-10-23 2005-05-25 Bayer Cropscience Ag 1,3-Dimethylbutylcarboxanilide
ATE541042T1 (de) 2004-03-05 2012-01-15 Bayer Cropscience Ag Pflanzen mit reduzierter aktivität des stärkephosphorylierenden enzyms phosphoglucan- wasser-dikinase
AR048026A1 (es) 2004-03-05 2006-03-22 Bayer Cropscience Gmbh Procedimientos para la identificacion de proteinas con actividad enzimatica fosforiladora de almidon
AR048025A1 (es) 2004-03-05 2006-03-22 Bayer Cropscience Gmbh Plantas con actividad aumentada de una enzima fosforilante del almidon
AR048024A1 (es) 2004-03-05 2006-03-22 Bayer Cropscience Gmbh Plantas con actividad aumentada de distintas enzimas fosforilantes del almidon
US7432082B2 (en) 2004-03-22 2008-10-07 Basf Ag Methods and compositions for analyzing AHASL genes
US20060010514A1 (en) 2004-06-16 2006-01-12 Basf Plant Science Gmbh Polynucleotides encoding mature AHASL proteins for creating imidazolinone-tolerant plants
DE102004029763A1 (de) 2004-06-21 2006-01-05 Bayer Cropscience Gmbh Pflanzen, die Amylopektin-Stärke mit neuen Eigenschaften herstellen
DE102004035137A1 (de) * 2004-07-20 2006-02-16 Bayer Cropscience Gmbh Wirkstoffe zur Steigerung der Pathogenabwehr in Pflanzen und Methoden zu ihrer Auffindung
US7807882B2 (en) 2004-07-30 2010-10-05 Basf Agrochemical Products B.V. Herbicide-resistant sunflower plants, polynucleotides encoding herbicide-resistant acetohydroxyacid synthase large subunit proteins, and methods of use
EP1776462A4 (fr) 2004-08-04 2010-03-10 Basf Plant Science Gmbh Séquences ahass de monocotylédone et leurs méthodes d'utilisation
ES2340183T3 (es) 2004-08-18 2010-05-31 Bayer Cropscience Ag Plantas con mayor actividad plastidica del enzima r3 fosforilante de almidon.
US8030548B2 (en) 2004-08-26 2011-10-04 Dhara Vegetable Oil And Foods Company Limited Cytoplasmic male sterility system for Brassica species and its use for hybrid seed production in indian oilseed mustard Brassica juncea
PL1805312T3 (pl) 2004-09-23 2009-12-31 Bayer Ip Gmbh Sposoby i środki do wytwarzania hialuronianu
AR051690A1 (es) 2004-12-01 2007-01-31 Basf Agrochemical Products Bv Mutacion implicada en el aumento de la tolerancia a los herbicidas imidazolinona en las plantas
EP1672075A1 (fr) 2004-12-17 2006-06-21 Bayer CropScience GmbH Plantes transformées exprimant un dextrane sucrase et synthétisant un amidon modifie
EP1679374A1 (fr) 2005-01-10 2006-07-12 Bayer CropScience GmbH Plantes transformées exprimant un mutane sucrase et synthétisant un amidon modifie
JP2006304779A (ja) 2005-03-30 2006-11-09 Toyobo Co Ltd ヘキソサミン高生産植物
EP1707632A1 (fr) 2005-04-01 2006-10-04 Bayer CropScience GmbH Amidon de pomme de terre cireux phosphorylé
EP1710315A1 (fr) 2005-04-08 2006-10-11 Bayer CropScience GmbH Amidon à forte teneur en phosphate
ATE439449T1 (de) 2005-06-15 2009-08-15 Bayer Bioscience Nv Verfahren zum erhöhen der widerstandsfähigkeit von pflanzen gegen hypoxische bedingungen
CN101203612B (zh) 2005-06-24 2013-03-20 拜尔作物科学公司 改进植物细胞壁反应性的方法
AR054174A1 (es) 2005-07-22 2007-06-06 Bayer Cropscience Gmbh Sobreexpresion de sintasa de almidon en vegetales
WO2007024782A2 (fr) 2005-08-24 2007-03-01 Pioneer Hi-Bred International, Inc. Compositions assurant une tolerance a de multiples herbicides et methodes d'utilisation
WO2007027777A2 (fr) 2005-08-31 2007-03-08 Monsanto Technology Llc Sequences nucleotidiques codant des proteines insecticides
CA2624496A1 (fr) 2005-10-05 2007-04-12 Bayer Cropscience Ag Plantes a production accrue de hyaluronane ii
CA2624592C (fr) 2005-10-05 2016-07-19 Bayer Cropscience Ag Plantes exprimant de la glutamine fructose-6-phosphate amidotransferase avec une production d'hyaluronan accrue
PL1951030T3 (pl) 2005-10-05 2015-07-31 Bayer Ip Gmbh Udoskonalone sposoby i środki do wytwarzania hialuronianu
JP2007186434A (ja) 2006-01-12 2007-07-26 Astellas Pharma Inc 医薬組成物
EP1987717A1 (fr) * 2007-04-30 2008-11-05 Bayer CropScience AG Pyridinecarboxamide, agent phytoprotecteur la comportant, son procédé de fabrication et son utilisation
WO2013037955A1 (fr) 2011-09-16 2013-03-21 Bayer Intellectual Property Gmbh Utilisation d'acylsulfonamides pour améliorer le rendement de végétaux
EP2589293A1 (fr) * 2011-11-03 2013-05-08 Bayer CropScience AG Compositions herbicides phytoprotectrices comprenant des amides d'acide carbonique de N-(tétrazol-5-yl) et N-(triazol-5-yl)aryle

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2015004040A1 *

Also Published As

Publication number Publication date
CN105530814A (zh) 2016-04-27
WO2015004040A1 (fr) 2015-01-15
US20160150782A1 (en) 2016-06-02
AU2014289341A1 (en) 2016-01-28
JP2016525510A (ja) 2016-08-25
CA2917559A1 (fr) 2015-01-15
MX2016000141A (es) 2016-03-01
AR096827A1 (es) 2016-02-03
EA201600097A1 (ru) 2016-06-30

Similar Documents

Publication Publication Date Title
EP3051946B1 (fr) Utilisation de dihydrooxindolylsulfonamides substitués ou de leurs sels pour augmenter la tolérance au stress dans des plantes
WO2014037340A1 (fr) Utilisation de 2-amidobenzimidazoles, de 2-amidobenzoxazoles et de 2-amidobenzothiazoles substitués ou de leurs sels comme principes actifs contre le stress abiotique des plantes
WO2013041602A1 (fr) Utilisation de dérivés d'acide 1-phényl-pyrazol-3-carboxylique à substitution en position 4 en tant qu'agents actifs contre le stress abiotique chez les végétaux
EP2658376A1 (fr) Utilisation d'acides sulfonamido-carboxyliques spirocycliques substitués, de leurs esters d'acide carboxylique, de leurs amides d'acide carboxylique et de leurs carbonitriles ou de leurs sels pour augmenter la tolérance au stress chez des plantes.
EP2729007A1 (fr) Utilisation d'isoquinoléinones, d'isoquinoléinediones, d'isoquinoléinetriones et de dihydroisoquinoléinones substituées ou de leurs sels comme principes actifs contre le stress abiotique des plantes
WO2012139890A1 (fr) 5-(cyclohex-2-én-1-yl)-penta-2,4-diènes et 5-(cyclohex-2-én-1-yl)-pent-2-èn-4-ines substitués en tant que principes actifs contre le stress abiotique des végétaux
EP3325446A1 (fr) Hydrazides substitués d'acide arylcarboxylique et hétéroarylcarboxylique ou leurs sels, et leur utilisation pour accroître la tolérance au stress chez les végétaux
WO2015004040A1 (fr) Utilisation de pyridonecarboxamides sélectionnés ou de leurs sels en tant que substances actives pour lutter contre le stress abiotique des végétaux
WO2014086751A1 (fr) Utilisation de 1-(aryléthinyl)-cyclohexanols, 1-(hétéroaryléthinyl)-cyclohexanols, 1-(hétérocyclyléthinyl)-cyclohexanols et 1-(cyloalcényléthinyl)-cyclohexanols substitués comme principes actifs contre le stress abiotique des plantes
WO2014037313A1 (fr) Utilisation de benzodiazepinones et de benzazepinones substituées ou de leurs sels comme principes actifs contre le stress abiotique des plantes
WO2015155154A1 (fr) Utilisation de oxo-tétrahydro-quinolinyl-sulfonamides substitués ou de leurs sels pour augmenter la tolérance des plantes au stress
WO2016096942A1 (fr) Utilisation de pyridone-carboxamides sélectionnés ou de leurs sels comme principes actifs contre le stress abiotique des plantes
WO2017009321A1 (fr) Amides substitués d'acide phosphonique et d'acide oxotétrahydrochinolinylphosphique, ou leurs sels et leur utilisation pour accroître la tolérance au stress chez les végétaux
JP2016518353A (ja) 新規トリアゾール誘導体
WO2017012965A1 (fr) Hydrazides substitués d'acide hétéroarylcarboxylique ou leurs sels, et leur utilisation pour accroître la tolérance au stress chez les végétaux
WO2016128365A1 (fr) 1-cycloalkyl-2-oxotétrahydrochinolin-6-yl-sulfonamides substitués ou leurs sels et leur utilisation pour accroître la tolérance au stress chez les végétaux
WO2019025153A1 (fr) Utilisation de n-sulfonyl-n'-aryldiaminoalcanes et de n-sulfonyl-n'-hétéroaryldiaminoalcanes substitués ou de leurs sels pour accroître la tolérance au stress chez les plantes
WO2018108627A1 (fr) Utilisation d'indolinylméthylsulfonamides substitués ou de leurs sels pour accroître la tolérance au stress chez les plantes
WO2017012922A1 (fr) Hydrazides cycliques substitués d'acide arylcarboxylique et hétéroarylcarboxylique ou leurs sels, et leur utilisation pour accroître la tolérance au stress chez les végétaux
EP2510786A1 (fr) Dérivés de prop-2-yn-1-ol et prop-2-en-1-ol substitués
AU2015289278A1 (en) Substituted vinyl and alkynyl cyanocycloalkanols and vinyl and alkynyl cyanoheterocycloalkanols as active agents against abiotic plant stress
EP3172187A1 (fr) Cyano-cycloalkylpenta-2,4-diènes, cyano-cycloalkylpent-2-èn-4-ynes, cyano-hétérocyclylpenta-2,4-diènes et cyano-hétérocyclylpent-2èn-4-ynes substitués utilisés comme principes actifs contre le stress abiotique des plantes
EP3332645A1 (fr) Utilisation de pyrimidinedione ou ses sels respectifs en tant qu'agent contre l'agression abiotique des plantes
EP2646418B1 (fr) Dérivés de pyrimidine et leur utilisation comme agents parasiticides.

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20160209

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

AX Request for extension of the european patent

Extension state: BA ME

DAX Request for extension of the european patent (deleted)
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20160908